(2S,6R)-2-Hydroxymethyl-6-methyl-piperidine-1-carboxylic acid benzyl ester | 142698-24-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,6R)-2-Hydroxymethyl-6-methyl-piperidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (2S,6R)-2-(hydroxymethyl)-6-methylpiperidine-1-carboxylate
• CAS: 142698-24-6
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: GRDSAVYKYLYLGF-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,6R)-2-Hydroxymethyl-6-methyl-piperidine-1-carboxylic acid benzyl ester 在 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (2R,6S)-2-Methyl-6-((E)-propenyl)-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  A New Procedure for Construction of 2,6-trans-Disubstituted Piperidines Using Osmium-catalyzed Asymmetric Dihydroxylation: Application to the Synthesis of (+)-Epidihydropinidine and (+)-Solenopsin A1

  摘要：

  An asymmetric synthesis of (+)-epidihydropinidine (1) and (+)-solenopsin A (2) has been achieved by starting with the Sharpless asymmetric dihydroxylation of the alpha-amino acid-derived N-alkenylurethanes (3) followed by subsequent aminocyclization.

  DOI：

  10.3987/com-94-6803
• 作为产物：
  描述：

  [(R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-1-methyl-hexyl]-carbamic acid benzyl ester 在 palladium dihydroxide 盐酸 、 sodium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (2S,6R)-2-Hydroxymethyl-6-methyl-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  A New Procedure for Construction of 2,6-trans-Disubstituted Piperidines Using Osmium-catalyzed Asymmetric Dihydroxylation: Application to the Synthesis of (+)-Epidihydropinidine and (+)-Solenopsin A1

  摘要：

  An asymmetric synthesis of (+)-epidihydropinidine (1) and (+)-solenopsin A (2) has been achieved by starting with the Sharpless asymmetric dihydroxylation of the alpha-amino acid-derived N-alkenylurethanes (3) followed by subsequent aminocyclization.

  DOI：

  10.3987/com-94-6803

文献信息

• A chirospecific synthesis of (−)-pinidine
  作者：Hiroki Takahata、Hiroshi Bandoh、Minori Hanayama、Takefumi Momose

  DOI：10.1016/s0957-4166(00)82292-2

  日期：1992.5

  A chirospecific synthesis of thecis-2,6-dialkylpieperidine alkaloids1 and2 has been achieved in eight steps (23%) and six steps (32%) from the known iodide3, respectively.

  从已知的碘化物3分别以八步（23％）和六步（32％）实现了顺式-2,6-二烷基哌啶生物碱1和2的手性合成。
• A New Procedure for Construction of 2,6-trans-Disubstituted Piperidines Using Osmium-catalyzed Asymmetric Dihydroxylation: Application to the Synthesis of (+)-Epidihydropinidine and (+)-Solenopsin A1
  作者：Hiroki Takahata、Kumiko Inose、Naomi Araya、Takefumi Momose

  DOI：10.3987/com-94-6803

  日期：——

  An asymmetric synthesis of (+)-epidihydropinidine (1) and (+)-solenopsin A (2) has been achieved by starting with the Sharpless asymmetric dihydroxylation of the alpha-amino acid-derived N-alkenylurethanes (3) followed by subsequent aminocyclization.